Trifluoroacetic acid → HCID 178515292, compound

HRID 1670274Notes

Reaction equation

HRID 1670274 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9](O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]=1[OH:8].C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>C(Cl)Cl>[CH2:9]([C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[C:7]=1[OH:8])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 1785152933-Bromo-5-(hydroxy(phenyl)methyl)pyridin-4-ol

Product 1

HCID 178515292HCID 178515292, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-bromo-5-(hydroxy(phenyl)methyl)pyridin-4-ol (2.55 g, 91 mmol), TFA (16 mL) and Et3SiH in CH2Cl2 (30 mL) was stirred at rt for 10 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel eluting with hexane/EtOAc/MeOH/600:300:50 followed by hexane/EtOAc/MeOH/400:400:50:10 to afford an impure product which was triturated with a small amount of MeOH and Et2O to obtain the desired product (255 mg, 10%) as a white solid. 1H NMR (DMSO-d6) δ 11.75 (br s, 1H), 8.13 (s, 1H), 7.54 (s, 1H), 7.26-7.14 (m, 5H), 2.49 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel eluting with hexane/EtOAc/MeOH/600:300:50
  3. customto afford an impure product which
  4. customwas triturated with a small amount of MeOH and Et2O

Sources & evidence

ORD record
ord-286b2bd8e76f4ec4916d26913bc70e4e
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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